2-Nitrophenylboronic acid Chemical Properties

Melting point:

155-160°C

Boiling point:

374.8±44.0 °C(Predicted)

Density 

1.40±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol,Ether,Ethanol

pka

7.83±0.53(Predicted)

form 

Crystalline Powder

color 

White to off-white

BRN 

3032097

InChI

InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H

InChIKey

SFUIGUOONHIVLG-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1[N+]([O-])=O)(O)O

CAS DataBase Reference

5570-19-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

29319090

MSDS

• Language:English Provider:ALFA

2-Nitrophenylboronic acid Usage And Synthesis

Chemical Properties

White to orange to brown solid

Uses

Boronic acid catalyst used for:

• Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides
• Transposition of allylic alcohols and Meyer-Schuster rearrangements

• Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates
• Copper-catalyzed halogenation
• Oxidative arylation of aminopyrazolyl disulfides

Synthesis

Using phenylboronic acid as starting material, nitric acid (126 g, 2 mol) and sodium nitrite (0.04 mol) were added dropwise to the reaction system and the reaction temperature was controlled at 45 °C. The reaction mixture was reacted with dimethylformamide (15 mol) under stirring conditions. Upon completion of the reaction, the mixture was poured completely into ice water, concentrated to a small volume, cooled and allowed to stand until a solid precipitate precipitated. The solid was separated by filtration and washed with ice water, and the final product 2-nitrophenylboronic acid 165.3 g was collected in 99.0% molar yield and >99.5% HPLC purity.

References

[1] Patent: CN104788484, 2017, B. Location in patent: Paragraph 0026-0039
[2] Patent: CN103214489, 2016, B. Location in patent: Paragraph 0061-0062
[3] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 46
[4] Synlett, 2002, # 3, p. 477 - 479
[5] Journal of Organometallic Chemistry, 2003, vol. 680, # 1-2, p. 263 - 270

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